Skip to main content

Part of the book series: Antibiotics ((ANTIBIOTICS,volume 6))

Abstract

Neothramycin has been isolated from Streptomyces MC916-C4 in the laboratory of Dr. Hamao Umezawa(Takeuchi et al., 1976). It is a potent antitumor antibiotic of the pyrrolo(l,4)benzodiazepine group, which anthramycin (cf. a review by, Kohn, 1975), sibiromycin (see a review by Gause, 1975), tomaymycin (Arimaet al., 1972) and mazethramycin (Kunimotoet al., 1980) belong to. Neothramycin1 contains two stereoisomers A and B in nearly equal amounts. The structural elucidation and total synthesis have been reported by Miyamoto et al. (1977). Both antibiotics are hydrated within 60 min after being dissolved in water, forming the 10-hydro-ll-hydroxyl-derivatives (Fig. 1). The hydroxyl groups at C-3 and C-ll epimerize in aqueous solution.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Arima K, Kohsaka M, Tamura G, Imanaka H, Sakai H (1972) Studies 011 tomaymycin, a new antibiotic. I. Isolation and properties of tomaymycin. J Antibiot (Tokyo) 24: 437–444

    Google Scholar 

  • Gause GF (1975) Sibiromycin. In: Corcoran JW, Hahn FE (eds) Antibiotics. Mechanism of action of antimicrobial and antitumor agents, vol III, pp 269–273. Springer, Berlin Heidelberg New York

    Google Scholar 

  • Hisamatsu T, Uchida S, Takeuchi T, Ishizuka M, Umezawa H (1980) Antitumor effect of a new antibiotic, neothramycin. Gann 71: 308–312

    PubMed  CAS  Google Scholar 

  • Hurley LH (1977) Pyrrolo(l,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J Antibiot (Tokyo) 30: 349–370

    CAS  Google Scholar 

  • Hurley LH, Petrusek R (1979) Proposed structure of the anthramycin-DNA adduct. Nature 282: 529–531

    Article  PubMed  CAS  Google Scholar 

  • Hurley LH, Rokem JS, Petrusek RL (1980) Proposed structures of the pyrrolo(l,4)benzodiazepine antibiotic-deoxyribonucleic acid adducts. Biochem Pharmacol 29: 1307–1310

    Article  PubMed  CAS  Google Scholar 

  • Kohn KW (1975) Anthramycin. In: Corcoran JW, Hahn FE (eds) Antibiotics. Mechanism of action of antimicrobial and antitumor agents, vol III, pp 3–11. Springer, Berlin Heidelberg New York

    Google Scholar 

  • Kunimoto S, Masuda T, Kobayashi N, Hamada M, Naganawa H, Miyamoto M, Takeuchi T, Umezawa H (1980) Mazethramycin, a new member of anthramycin group antibiotics. J Antibiot (Tokyo) 33: 665–667

    CAS  Google Scholar 

  • Maruyama IN, Suzuki H, Tanaka N (1978) Mechanism of action of neothramycin. I. The effect on macromolecular syntheses. J Antibiot (Tokyo) 31: 761–768

    Google Scholar 

  • Maruyama IN, Tanaka N, Kondo S, Umezawa H (1979) Mechanism of action of neothramycin. II. Interaction with DNA. J Antibiot (Tokyo) 32: 928–934

    Google Scholar 

  • Maruyama IN, Tanaka N, Kondo S, Umezawa H (1981 a) Fluorospectrometric studies on neothramycin and its reaction with DNA. J Antibiot (Tokyo) 34: 427–435

    Google Scholar 

  • Maruyama IN, Tanaka N, Kondo S, Umezawa H (1981 b) Structure of a neothramycin-2-deoxyguan- osine adduct. Biochem Biophys Res Commun 98: 970–975

    Google Scholar 

  • Miyamoto M, Kondo S, Naganawa H, Maeda K, Ohno M, Umezawa H (1977) Structure and synthesis of neothramycin. J Antibiot (Tokyo) 30: 340–343

    CAS  Google Scholar 

  • Nishioka Y, Beppu T, Kohsaka M, Arima K (1972) Mode of action of tomaymycin. J Antibiot (Tokyo) 25: 660–667

    CAS  Google Scholar 

  • Olmsted J III, Kearns DR (1977) Mechanism of ethidium fluorescence enhancement on binding to nucleic acids. Biochemistry 16: 3647–3654

    Article  PubMed  CAS  Google Scholar 

  • Petrusek RL, Anderson GL, Garner TF, Fannin QL, Kaplan DJ, Zimmer SG, Hurley LH (1981) Pyrrolo(l,4)benzodiazepine antibiotics. Proposed structures and characteristics of the in vitro deoxyribonucleic acid adducts of anthramycin, tomaymycin, sibiromyin, and neothramycins A and B. Biochemistry 20: 1111–1119

    Google Scholar 

  • Takeuchi T, Miyamoto M, Ishizuka M, Naganawa H, Kondo S, Hamada M, Umezawa H (1976) Neothramycins A and B, new antitumor antibiotics. J Antibiot (Tokyo) 29: 93–96

    CAS  Google Scholar 

  • Waring M (1975) Ethidium and propidium. In: Corcoran JW, Hahn FE (eds) Antibiotics. Mechanism of action of antimicrobial and antitumor agents, vol III, pp 141–165. Springer, Berlin Heidelberg New York

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1983 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

Tanaka, N. (1983). Neothramycin. In: Hahn, F.E. (eds) Modes and Mechanisms of Microbial Growth Inhibitors. Antibiotics, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68946-8_9

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-68946-8_9

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68948-2

  • Online ISBN: 978-3-642-68946-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics